3,6-Diethoxy-2,5-dihydropyrazine → 3,6-Diethoxy-2-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyl}-2,5-dihydropyrazine

HRID 252411Notes

Reaction equation

HRID 252411 reaction equation
C([Li])CCC.[CH2:6]([O:8][C:9]1[CH2:10][N:11]=[C:12]([O:15][CH2:16][CH3:17])[CH2:13][N:14]=1)[CH3:7].Br[CH2:19][CH:20]([CH:37]([CH3:39])[CH3:38])[CH2:21][C:22]1[CH:31]=[C:30]2[C:25]([CH:26]=[CH:27][CH:28]=[C:29]2[O:32][CH2:33][CH2:34][O:35][CH3:36])=[CH:24][CH:23]=1>O1CCCC1>[CH2:6]([O:8][C:9]1[CH:10]([CH2:19][CH:20]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[C:30](=[C:29]([O:32][CH2:33][CH2:34][O:35][CH3:36])[CH:28]=[CH:27][CH:26]=3)[CH:31]=2)[CH:37]([CH3:38])[CH3:39])[N:11]=[C:12]([O:15][CH2:16][CH3:17])[CH2:13][N:14]=1)[CH3:7]

Participants

5

Reactant 3

HCID 111267023,6-Diethoxy-2,5-dihydropyrazineHCID 668884037-(2-Bromomethyl-3-methylbutyl)-1-(2-methoxyethoxy)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 668877873,6-Diethoxy-2-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyl}-2,5-dihydropyrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

3.03 ml of n-butyllithium (1.6M in hexane) are added dropwise at −40° C. to the suspension of 0.884 g of 3,6-diethoxy-2,5-dihydropyrazine in 12 ml of tetrahydrofuran. After 20 minutes, a solution of 1.265 g of 7-(2-bromomethyl-3-methylbutyl)-1-(2-methoxyethoxy)naphthalene in 5 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred further at −40″C. for 30 minutes, then warmed to −20° C. over 1 hour. After 18 hours, the reaction mixture is concentrated by evaporation—the residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2×)—the combined organic phases are washed successively with water (2×) and brine, dried over sodium sulphate and concentrated by evaporation. The crude title compound is identified on the basis of the Rf value from the residue.

Workup

  1. waitfor 30 minutes
  2. waitAfter 18 hours
  3. concentrationthe reaction mixture is concentrated by evaporation—the residue
  4. customis partitioned between ethyl acetate and water
  5. extractionThe aqueous phase is extracted with ethyl acetate (2×)—the combined organic phases
  6. washare washed successively with water (2×) and brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-44ff97a902354401ac764936c965ac76
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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